Galois connections are a foundational tool for structuring abstraction in semantics, and their use lies at the heart of the theory of abstract interpretation. Yet, mechanization of Galois connections using proof assistants remains limited to restricted modes of use, preventing their general application in mechanized metatheory and certified programming. This paper presents constructive Galois connections, a variant of Galois connections that is effective both on paper and in proof assistants; is complete with respect to a large subset of classical Galois connections; and enables more general reasoning principles, including the “calculational” style advocated by Cousot. To design constructive Galois connections, we identify a restricted mode of use of classical ones which is both general and amenable to mechanization in dependently typed functional programming languages. Crucial to our metatheory is the addition of monadic structure to Galois connections to control a “specification effect.” Effectful calculations may reason classically, while pure calculations have extractable computational content. Explicitly moving between the worlds of specification and implementation is enabled by our metatheory. To validate our approach, we provide two case studies in mechanizing existing proofs from the literature: the first uses calculational abstract interpretation to design a static analyzer, and the second forms a semantic basis for gradual typing. Both mechanized proofs closely follow their original paper-and-pencil counterparts, employ reasoning principles not captured by previous mechanization approaches, support the extraction of verified algorithms, and are novel.